GB994382A - Preparation of dicyanoethylated fatty amines - Google Patents
Preparation of dicyanoethylated fatty aminesInfo
- Publication number
- GB994382A GB994382A GB25320/62A GB2532062A GB994382A GB 994382 A GB994382 A GB 994382A GB 25320/62 A GB25320/62 A GB 25320/62A GB 2532062 A GB2532062 A GB 2532062A GB 994382 A GB994382 A GB 994382A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dicyanoethylated
- heating
- preparation
- catalyst
- fatty amines
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001412 amines Chemical class 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 239000003760 tallow Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- KKAOKGAELKHSOH-UHFFFAOYSA-N 2-(aminomethyl)propanedinitrile Chemical class NCC(C#N)C#N KKAOKGAELKHSOH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- -1 C22 primary amine Chemical class 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Dicyanoethylated fatty amines are made by heating under pressure a C8 to C22 primary amine with more than two mols. of acrylonitrile per mol. of amine, at preferably 100 DEG to 190 DEG C. and under pressure, in the presence of a proton transfer catalyst which may be water, morpholine or methanol, the preferred catalyst being water and morpholine. The process may be carried out by heating first to 100 DEG C. to add one cyanoethyl group and then to 135 DEG to 180 DEG C. to add the second group. Preferred starting amines are derived from tallow, soya or coco fatty acids. The examples describe the use of heating in two stages in the preparation of the dicyanoethylamines of coco, soya and tallow and contain a comparative run without the use of the essential catalyst.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US121326A US3264341A (en) | 1961-07-03 | 1961-07-03 | Preparation of dicyanoethylated fatty amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB994382A true GB994382A (en) | 1965-06-10 |
Family
ID=22395957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25320/62A Expired GB994382A (en) | 1961-07-03 | 1962-07-02 | Preparation of dicyanoethylated fatty amines |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3264341A (en) |
| FR (1) | FR1328088A (en) |
| GB (1) | GB994382A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3364248A (en) * | 1964-09-22 | 1968-01-16 | Armour & Co | Novel dicyanoethylfattydiamines of fatty acids |
| CN113372241B (en) * | 2020-03-09 | 2023-01-13 | 万华化学集团股份有限公司 | Method for synthesizing dinitrile ethyl tertiary amine by aliphatic primary amine one-step method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2787633A (en) * | 1954-03-01 | 1957-04-02 | Gen Mills Inc | Acceleration of fatty amine addition reactions |
| US2982781A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and- beta-aminoesters |
| US3028415A (en) * | 1959-05-01 | 1962-04-03 | Gen Mills Inc | Preparation of acrylonitrile di-adducts of primary aliphatic amines |
| US3158643A (en) * | 1961-05-05 | 1964-11-24 | Gen Mills Inc | Cyanoethylated aminohydroxy amines |
-
1961
- 1961-07-03 US US121326A patent/US3264341A/en not_active Expired - Lifetime
-
1962
- 1962-06-28 FR FR7445A patent/FR1328088A/en not_active Expired
- 1962-07-02 GB GB25320/62A patent/GB994382A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1328088A (en) | 1963-05-24 |
| US3264341A (en) | 1966-08-02 |
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